6-(3-Iodophenyl)-6-oxohexanenitrile , CAS No.898767-95-8

CAS: 898767-95-8 Cat. No.: I966668 Formula: C₁₂H₁₂INO Peso molecolare: 313.138 PubChem CID: 24723851

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

• Sorrisi canonici: C1=CC(=CC(=C1)I)C(=O)CCCCC#N
• IUPAC Name: 6-(3-iodophenyl)-6-oxohexanenitrile
• InChIKey: DECOPSDWOKBWGC-UHFFFAOYSA-N
• INCHI: 1S/C12H12INO/c13-11-6-4-5-10(9-11)12(15)7-2-1-3-8-14/h4-6,9H,1-3,7H2
• Isomeri SMILES: C1=CC(=CC(=C1)I)C(=O)CCCCC#N
• PubChem CID: 24723851
• Peso molecolare: 313.138

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Carbonyl compounds
        • Level5 Ketones
          • Level6 Aryl ketones
            • Level7 Phenylketones
              • Level8 Alkyl-phenylketones

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Ketones - Aryl ketones - Phenylketones
• Direct Parent: Alkyl-phenylketones
• Alternative Parents: Butyrophenones Benzoyl derivatives Aryl alkyl ketones Iodobenzenes Aryl iodides Nitriles Organopnictogen compounds Organoiodides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Alkyl-phenylketone - Butyrophenone - Benzoyl - Aryl alkyl ketone - Halobenzene - Iodobenzene - Aryl halide - Aryl iodide - Monocyclic benzene moiety - Benzenoid - Nitrile - Carbonitrile - Organic nitrogen compound - Organohalogen compound - Organoiodide - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 313.130 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 312.996 Da
• Monoisotopic Mass: 312.996 Da
• Topological Polar Surface Area: 40.900 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 256.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

• No application protocols are provided for this catalog item. Typical usage is as a chemical building block in organic synthesis.
• For cross‑coupling or carbonyl transformations involving this substrate, refer to the Reaction Conditions and Synthetic Utility sections for general literature guidance and then adapt to your specific transformation.

Biological Roles

• This product is a synthetic organic building block intended for research and chemical synthesis. No endogenous biological role is associated with 6‑(3‑iodophenyl)‑6‑oxohexanenitrile.
• Literature context (general)
  • Aryl iodides and aryl‑alkyl ketone–nitrile frameworks appear as intermediates in the synthesis of ligands, radiolabel precursors (via iodine exchange), and diversified scaffolds for SAR studies, but this compound itself is not a known metabolite or biochemical cofactor.
• Research use only
  • Not for human or veterinary use. Any biological testing should be conducted under appropriate approvals and using validated controls. Consult SDS for handling in biological labs.

Buffer Applications

• Not typically applicable. This compound is a neutral, sparingly water‑soluble organic building block and is not used as a buffering agent.
• For aqueous work, dissolve in a miscible organic co‑solvent (e.g., DMSO, MeCN) before dilution into buffer if required for assays, keeping final organic content within assay tolerance.

Green Alternatives

• Strategy for greener synthesis using this building block
  • Prefer aqueous or bio‑based solvent systems for cross‑couplings (e.g., water/EtOH with TPGS‑750‑M micelles) over DMF/DMAc when feasible.
  • Use 2‑MeTHF or CPME in place of THF/MTBE for enolate and reduction chemistry to improve safety and lifecycle metrics.
  • Apply heterogeneous or ligand‑efficient Pd/Ni catalysts at ppm levels; flow or photoredox nickel catalysis can lower precious‑metal use for Ar–I activation.
• Example comparisons (general, literature)
  • Solvent choice in Suzuki coupling:
    • Conventional: DMF, dioxane, toluene (excellent performance; higher EHS burden).
    • Greener: water or 95:5 water/EtOH with nonionic surfactant; often comparable rates for Ar–I substrates at 30–60 °C.
  • Base selection:
    • Conventional: Cs2CO3, K3PO4 (effective, variable sourcing impacts).
    • Greener: K2CO3, Na2CO3, or aqueous carbonate; balance rate vs. waste.
  • Workup/purification:
    • Replace chlorinated solvents in extraction with EtOAc or bio‑esters when possible; use minimal solvent and crystallization instead of chromatography if attainable.
• Tradeoffs
  • Ar–I offers best reactivity but embeds iodine (LCA burden); if reactivity margin allows, preparing the aryl boronate and coupling from a bromide may reduce halogen mass—however, this alters the starting material and chemistry.
  • Water‑rich media may hydrolyze nitriles under harsh conditions; maintain near‑neutral pH for stability.

Pharmaceutical Uses

• Formulation/excipient role: none. This material is supplied as a research chemical/building block and is not an approved excipient.
• Possible R&D roles (general)
  • Intermediate in medicinal chemistry routes to target compounds, prodrugs, or linkers due to its orthogonal functional handles (Ar–I, ketone, nitrile).
• Compliance
  • No pharmacopeial monographs are implied. For GMP or clinical manufacturing, a different sourcing and qualification pathway would be required.

Physical Properties

• Item-specific specifications (for this catalog item)
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Purity/grade: Not specified for this item; refer to CoA/Spec Sheet.
  • Water/peroxide/metal limits, UV cutoff, RI: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/computed (general expectations for aryl‑iodo aryl‑alkyl ketone bearing a terminal nitrile)
  • Physical state: typically a pale solid or viscous oil for similar aryl‑iodo aryl‑alkyl ketones with C≡N; confirm on CoA.
  • Solubility profile (qualitative): good solubility in moderately polar aprotic solvents (e.g., DMF, DMSO, MeCN, EtOAc), limited solubility in water; increased solubility in chlorinated solvents and aromatic hydrocarbons (literature trend for Ar–I ketones).
  • Acid/base: neutral organic compound; no titratable groups under normal conditions (nitrile and ketone are non‑basic/weakly basic only in superacids).
  • Volatility: low to moderate; aryl iodides and aryl‑alkyl ketones typically have elevated boiling points and low vapor pressures.
• Important
  • Do not use literature expectations as specifications. For method development or regulatory work, verify exact values (mp/bp, density, solubilities) on the product CoA/SDS.

Quality and Grades

• Item-specific
  • Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
• Guidance on interpreting grades (general)
  • Research grade: suitable for most synthetic and discovery applications; may not control trace metals or UV impurities tightly enough for analytical quantitation.
  • Purified/≥98% organic building blocks typically support cross‑coupling and condensations reliably; residual halides, iodine, and water can influence catalyst performance.
• QC considerations for this structural class
  • Ar–I content and identity typically verified by 1H/13C NMR, HRMS, and sometimes 127I NMR; GC/LC area% for purity; water by KF if needed.
  • Residual iodide or iodine can cause elevated baseline in UV HPLC; low-UV grades may be preferred for analytical work. If HPLC or photochemical steps are planned, request UV cutoff/absorbance data where relevant.
  • For cross-coupling applications, trace metal content (Pd/Cu/Ni) is usually not controlled in the starting aryl iodide unless specified; pre‑treat or adjust catalyst loading accordingly.
• Documentation
  • For exact assay, residual solvents, and impurity profile, consult the lot-specific CoA/SDS.

Reaction and Applications

• Cross‑coupling via the aryl iodide
  • Suzuki–Miyaura (with boronic acids/esters), Sonogashira (terminal alkynes), Buchwald–Hartwig (amines), and carbonylative couplings are facilitated by the high reactivity of Ar–I.
  • Practical tips: use freshly degassed solvent; keep water content controlled for moisture‑sensitive partners; 0.5–2 mol% Pd is often sufficient for Ar–I at 25–80 °C; micellar conditions (TPGS‑750‑M) can enable aqueous couplings.
• Ketone reactivity at C6
  • Enolate chemistry: α‑functionalization (halogenation, alkylation), aldol or Claisen‑type condensations; control enolate geometry/chemoselectivity by base (LDA, NaHMDS) and solvent (THF, toluene/THF).
  • Reductions: selective ketone reduction (NaBH4, catalytic transfer hydrogenation) tolerates the nitrile; stronger hydrides (DIBAL‑H) risk nitrile reduction at low temperature—plan chemoselectivity accordingly.
• Nitrile as a handle
  • Hydrolysis to amide/acid (acidic or basic conditions, elevated temperature) or partial hydration to amidine/imidate under specific conditions; organometallic addition (RMgX/RLi) to give imines/ketimines followed by hydrolysis.
  • Cyclization strategies: nitrile can engage in intramolecular condensation or serve as a precursor to tetrazoles (via [3+2] with azide) in multi‑step sequences.
• Divergent elaboration
  • Orthogonal handles (Ar–I, C=O, C≡N) enable modular synthesis of heterocycles, bioisosteres, and linker‑bearing intermediates.
• Practicalities
  • Protect nitrile from prolonged strong base/acid at reflux if it must remain intact.
  • For cross‑couplings, iodide is advantageous; if undesired, Finkelstein‑type exchange to Ar–Br/Ar–Cl is uncommon—use direct metalation or convert post‑coupling as needed.

Reaction Conditions

• Cross‑coupling (general literature guidance for Ar–I)
  • Suzuki–Miyaura: Pd(PPh3)4 (0.5–1 mol%), K3PO4 (2–3 equiv), dioxane/H2O (4:1), 40–60 °C, 2–6 h; often >80% isolated yield for activated Ar–I.
  • Sonogashira: PdCl2(PPh3)2 (1 mol%), CuI (5 mol%), Et3N, THF or DMAc, 25–50 °C, 2–8 h; copper‑free systems with bulky ligands at 50–70 °C are alternatives.
  • Buchwald–Hartwig: Pd2(dba)3 (1–2 mol%), BINAP or XPhos, NaOtBu/K3PO4, toluene/dioxane, 60–90 °C.
• Carbonyl transformations
  • Reductive amination: ketone + amine (1.2–1.5 equiv), NaBH3CN or NaBH(OAc)3, MeOH/THF, 0–25 °C, 2–16 h; protect nitrile from strong acid.
  • Enolate alkylation: LDA (1.1–1.5 equiv) in THF at −78 to −20 °C, then electrophile; quench cautiously to avoid nitrile hydrolysis.
  • Baeyer–Villiger: mCPBA (1.5–2 equiv), DCM, 0–25 °C, 2–12 h to give the corresponding ester; watch for competitive oxidation of iodide under harsh conditions.
• Nitrile transformations
  • Hydrolysis to amide: aq. H2SO4 or HCl, reflux; to acid: extended time or stronger conditions; base‑promoted routes (NaOH, reflux) also common—consider iodide stability.
  • Hydrogenation to amine: Raney Ni or Pd/C, H2 (20–50 bar), alcohol solvent; ketone may also reduce—protect or sequence steps.
• Notes
  • Parameters above are representative literature ranges for the functional groups present, not specifications for this product. Optimize for your substrate, and verify compatibility with the aryl iodide and the dual carbonyl/nitrile functionality.

Safety and Handling

• Item-specific GHS (from Product Data)
  • Signal word: Not specified for this item; refer to SDS.
  • H‑statements: Not specified for this item; refer to SDS.
  • GHS classification/pictograms: Not specified for this item; refer to SDS.
• General hazards for structural class (literature/analog-based guidance; not a substitute for SDS)
  • May cause irritation to skin, eyes, and respiratory tract typical of neutral organic compounds; aryl iodides and nitriles can be harmful if swallowed or inhaled.
  • Combustible organic; avoid ignition sources.
  • Aryl iodides can undergo photolysis; protect from strong UV during storage/handling when feasible.
• PPE and engineering controls
  • Wear lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Work in a fume hood to control vapor/aerosol.
• Incompatibilities/precautions
  • Avoid strong oxidizers and strong bases during storage. Ketones can form enolates under strong base; nitriles can hydrolyze under strongly acidic or basic conditions at elevated temperature.
  • Avoid prolonged exposure to light and moisture. Keep container tightly closed.
• First-aid overview (consult SDS for details)
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; obtain medical advice if irritation continues.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Disposal
  • Dispose of contents/container in accordance with local regulations for halogenated organic wastes.

Solvent Selection

• Applicability: This product is an organic building block (aryl iodide bearing ketone and nitrile). Solvent choice is typically driven by the intended reaction (e.g., cross‑coupling, condensations) or by formulation/dissolution for analysis.
• Polarity/miscibility (literature expectations)
  • Likely highly soluble in polar aprotic media (DMF, DMSO, DMAc, NMP, MeCN) and good in chlorinated solvents (DCM, CHCl3) and ethyl acetate; moderately soluble in toluene/THF; poorly soluble in water.
• Typical use scenarios
  • Cross-coupling: DMF, DMAc, 2‑MeTHF, dioxane, or toluene with a base (K3PO4, Cs2CO3) provide good dissolution of Ar–I substrates.
  • Carbonyl chemistry (aldol/condensation): alcohols (MeOH/EtOH) or aprotic solvents (THF/MeCN) depending on base; avoid strong protic media if nitrile hydrolysis is a concern.
  • Purification: normal-phase silica using hexanes/EtOAc or toluene/EtOAc; for more polar behavior, include 0.1–1% TEA to minimize tailing of carbonyl compounds.
• Comparison notes
  • Versus less functionalized aryl iodides, the ketone and nitrile increase polarity, improving solubility in medium‑polarity solvents and potentially enabling higher concentrations in DMF/MeCN.
  • If catalyst solubility is limiting, co‑solvents (toluene/THF with DMF or i‑PrOH) can balance substrate and catalyst solubility.

Storage and Reconstitution

• Item-specific (from Product Data)
  • Storage conditions: Room temperature.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Practical guidance
  • Store tightly closed under inert atmosphere (e.g., nitrogen) if possible to minimize oxidation or moisture uptake. Protect from strong light to limit photolysis of the aryl iodide.
  • If solidification or partial crystallization occurs, gently warm to ambient and sonicate to homogenize before dispensing.
  • For solution preparation: dissolve the compound in a suitable anhydrous organic solvent (e.g., DMSO, DMF, MeCN, THF, or EtOAc) to prepare stock solutions; filter if necessary through PTFE.
  • Avoid repeated freeze–thaw of solutions; prepare single‑use aliquots. For long‑term solution storage, keep at 2–8 °C or −20 °C in amber vials, verifying stability experimentally.
• Stability note
  • Avoid prolonged exposure to strong acids/bases or aqueous media at elevated temperature to preserve the nitrile and aryl iodide functionalities.
• Always refer to the SDS and lot-specific CoA for authoritative storage and handling guidance.

Structure and Identity

• Item-specific (from Product Data)
  • Product name: 6-(3-Iodophenyl)-6-oxohexanenitrile (SKU: I966668)
  • CAS: 898767-95-8
  • InChIKey: 61064 (as provided; a full-length InChIKey was not supplied in the Product Data)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/structural interpretation (general)
  • Name analysis indicates a linear hexanenitrile backbone bearing an ω-ketone at C6 (6-oxo) that is arylated with a 3‑iodophenyl substituent on the carbonyl carbon.
  • Functional groups: aryl iodide (Ar–I), aryl–alkyl ketone (Ar–CO–), and terminal nitrile (–C≡N) separated by an aliphatic (CH2)n spacer.
  • 2D connectivity (verbal): a 3‑iodophenyl ring bonded to a carbonyl carbon; the carbonyl is attached to a pentamethylene chain terminating in a nitrile group. The aromatic ring is meta‑iodo relative to the carbonyl linkage.
  • Stereochemistry: none expected (acyclic, no stereogenic centers).
• Notes
  • The above interpretation is provided to aid users; confirm exact identifiers and structure on the product CoA/SDS for your specific lot.

Synthetic Utility

• Orthogonal functionality
  • Aryl iodide enables rapid diversification via Pd/Ni‑catalyzed cross‑couplings (C–C, C–N, C–O, C–S). The iodide may also be exploited in radical chemistry (e.g., Giese additions, Minisci‑type via photoredox after aryl radical generation).
  • Ketone allows enolate chemistry, reductive amination, oxime/hydrazone formation, Baeyer–Villiger oxidation (to an ester) with the chain retained, or Wittig/Julia–Kocienski olefination at the α‑position (after appropriate functionalization).
  • Nitrile can be transformed to amide/acid (hydrolysis), amine (catalytic hydrogenation), tetrazole (azide cycloaddition), or used as a directing group for C–H activation in certain metal‑catalyzed protocols.
• Retrosynthetic value
  • Serves as a convergent junction: the aryl iodide can be introduced late to retain coupling latitude; the ketone/nitrile chain can be installed via acylation (e.g., 3‑iodobenzoyl chloride equivalent) with a cyano‑alkyl organometallic synthon or via nitrile‑bearing acyl anion equivalents.
• Selectivity notes
  • Under basic conditions, prefer chemistries that avoid nitrile hydrolysis if the C≡N must persist. For reductions, choose hydride strength and solvent to favor C=O over C≡N.
  • Cross‑coupling conditions should be chosen to avoid α‑deprotonation/side reactions at the ketone if strongly basic media are used; milder bases (K3PO4, K2CO3) are often sufficient for Ar–I.

Target Specificity

• Not applicable. This product is a small‑molecule building block and is not an antibody, enzyme, or affinity reagent. No target specificity data are provided for this item.